Robert Grossman at his studio on Crosby Street in New York City, 1968.

Jan Welt/Courtesy of the Grossman Family

Robert Grossman, the artist and illustrator whose musician portraits and madcap political caricatures featured on the cover and in the pages of Rolling Stone, died March 15th at the age of 78. His son, Alex Emanuel Grossman, confirmed his death to The New York Times.

Grossman was born in Brooklyn, New York in 1940. His father, Joseph, worked in silk-screen printing. He attended Yale, where he got a taste of political satire by working on humor magazine The Yale Record. After graduation, he took a job assisting the art editor at The New Yorker.

He also embarked on his prolific freelance career, which included over 500 magazine covers for the New York Times, New York, New York Observer and The Nation, among others. He is also credited with creating one of the first black superheroes, a character named Captain Melanin that appeared in some of his 1960s comic strips, along with the iconic knotted-up airplane illustration featured on the poster for the 1980 comedy Airplane!

In addition to his accomplishments as an illustrator, Grossman also dabbled in music – during a short-lived career as a folk singer, he released an album titled Cosmo Alley Presents Bob Grossman. He received an Academy Award nomination in the Best Animated Short Film category in 1977 for his work on Jimmy The C. The short included a clay-animated version of President Jimmy Carter singing Ray Charles’ version of “Georgia on My Mind.”

But Grossman never stopped creating satirical political illustrations. During the 2008 campaign, he invented O-Man, a character based on President Obama, who faced off against Milt Rhomboid and Rich Gingnewt. More recently, Grossman posted short strips online titled “Twump and Pooty,” which detailed an exaggeratedly friendly relationship between President Trump and Vladimir Putin.

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Though some of his most famous caricatures took on right-wing politicians, Grossman said he was happy to lampoon anyone and everyone. “I don’t think cartoons are ever ‘for’ anything,” he told The New York Timesin 2008. “The idea is to ridicule everything, although you are free to guess for whom I am likely to vote when the time comes.”